Sannicolò Francesco, Mussini Patrizia R, Benincori Tiziana, Martinazzo Rocco, Arnaboldi Serena, Appoloni Giulio, Panigati Monica, Quartapelle Procopio Elsa, Marino Valentina, Cirilli Roberto, Casolo Simone, Kutner Wlodzimierz, Noworyta Krzysztof, Pietrzyk-Le Agnieszka, Iskierko Zofia, Bartold Katarzyna
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milano, Italy.
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100, Como, Italy.
Chemistry. 2016 Jul 25;22(31):10839-47. doi: 10.1002/chem.201504899. Epub 2016 Jun 20.
The racemate of an inherently chiral "spider-like" octathiophene monomer T83 , in which chirality is generated by torsion in its backbone, was synthesized. The racemate was resolved into configurationally stable antipodes by HPLC on a chiral stationary phase. Electrooxidation of the enantiomers resulted in materials displaying high enantiorecognition ability towards the antipodes of some chiral probes. Moreover, the T83 racemate demonstrated great aptitude to stimulate formation of 3D rigid architectures if used as a cross-linking monomer for molecular imprinting. This feature was exploited to devise a molecularly imprinted polymer-based chemosensor selective for a thymine-adenine oligonucleotide.
合成了一种具有固有手性的“蜘蛛状”八噻吩单体T83的外消旋体，其手性由主链中的扭转产生。通过在手性固定相上进行高效液相色谱法，将该外消旋体拆分为构型稳定的对映体。对映体的电氧化产生了对某些手性探针的对映体具有高对映体识别能力的材料。此外，如果将T83外消旋体用作分子印迹的交联单体，它表现出极大的促进三维刚性结构形成的能力。利用这一特性设计了一种对胸腺嘧啶-腺嘌呤寡核苷酸具有选择性的基于分子印迹聚合物的化学传感器。
